CA2504907C - Indoles useful in the treatment of androgen-receptor related diseases - Google Patents

Indoles useful in the treatment of androgen-receptor related diseases Download PDF

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Publication number
CA2504907C
CA2504907C CA2504907A CA2504907A CA2504907C CA 2504907 C CA2504907 C CA 2504907C CA 2504907 A CA2504907 A CA 2504907A CA 2504907 A CA2504907 A CA 2504907A CA 2504907 C CA2504907 C CA 2504907C
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CA
Canada
Prior art keywords
alkyl
nitrophenyl
pyridin
difluorophenyl
nitro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2504907A
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English (en)
French (fr)
Other versions
CA2504907A1 (en
Inventor
Pedro Harold Han Hermkens
Herman Thijs Stock
Neeltje Miranda Teerhuis
Johannes Petrus Maria Lommerse
Jaap Van Der Louw
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Sharp and Dohme BV
Original Assignee
Organon NV
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Filing date
Publication date
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Publication of CA2504907A1 publication Critical patent/CA2504907A1/en
Application granted granted Critical
Publication of CA2504907C publication Critical patent/CA2504907C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/16—Masculine contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/26—Androgens
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06—Antianaemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Endocrinology (AREA)
  • Diabetes (AREA)
  • Neurology (AREA)
  • Reproductive Health (AREA)
  • Rheumatology (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Neurosurgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Cardiology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pregnancy & Childbirth (AREA)
  • Psychiatry (AREA)
  • Vascular Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Obesity (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
CA2504907A 2002-11-07 2003-11-03 Indoles useful in the treatment of androgen-receptor related diseases Expired - Fee Related CA2504907C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US42457902P 2002-11-07 2002-11-07
EP02079648 2002-11-07
US60/424,579 2002-11-07
EP02079648.8 2002-11-07
PCT/EP2003/050783 WO2004041782A1 (en) 2002-11-07 2003-11-03 Indoles useful in the treatment of androgen-receptor related diseases

Publications (2)

Publication Number Publication Date
CA2504907A1 CA2504907A1 (en) 2004-05-21
CA2504907C true CA2504907C (en) 2011-10-11

Family

ID=42635437

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2504907A Expired - Fee Related CA2504907C (en) 2002-11-07 2003-11-03 Indoles useful in the treatment of androgen-receptor related diseases

Country Status (15)

Country Link
EP (1) EP1585727B1 (de)
JP (1) JP4643989B2 (de)
CN (1) CN100391944C (de)
AT (1) ATE469128T1 (de)
AU (1) AU2003301853B2 (de)
BR (1) BR0316020A (de)
CA (1) CA2504907C (de)
ES (1) ES2344836T3 (de)
NZ (1) NZ539657A (de)
PL (1) PL376728A1 (de)
RS (1) RS20050340A (de)
RU (1) RU2328484C2 (de)
TW (1) TWI310032B (de)
UA (1) UA79504C2 (de)
WO (1) WO2004041782A1 (de)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200602317A (en) * 2004-04-23 2006-01-16 Akzo Nobel Nv Novel androgens
DE102004047272A1 (de) * 2004-09-24 2006-04-06 Schering Ag Inhibitoren der löslichen Adenylatzyklase
DE102005027274A1 (de) * 2005-06-08 2006-12-14 Schering Ag Inhibitoren der löslichen Adenylatzyklase
US7417066B2 (en) 2005-06-08 2008-08-26 Schering Ag Inhibitors of soluble adenylate cyclase
CA2612723A1 (en) * 2005-06-24 2007-01-04 Eli Lilly And Company Tetrahydrocarbazole derivatives useful as androgen receptor modulators
WO2007073231A1 (en) * 2005-12-23 2007-06-28 Victor Lvovoch Limonov Agent for treating tumoral diseases, a method for the production thereof and a method for treating tumoral diseases
DE102006014324B4 (de) 2006-03-23 2009-01-08 Bayer Schering Pharma Aktiengesellschaft Inhibitoren der löslichen Adenylatzyklase
SI2656842T1 (sl) 2006-03-27 2016-10-28 The Regents Of The University Of California Modulator androgenih receptorjev za zdravljenje raka prostate in bolezni, povezanih z androgenimi receptorji
JP5275236B2 (ja) * 2006-09-29 2013-08-28 スミスクライン ビーチャム コーポレーション 置換されたインドール化合物
CA2716320C (en) 2008-02-22 2014-01-28 Radius Health, Inc. Selective androgen receptor modulators
US8268872B2 (en) 2008-02-22 2012-09-18 Radius Health, Inc. Selective androgen receptor modulators
RU2408592C2 (ru) * 2008-12-31 2011-01-10 Федеральное государственное образовательное учреждение высшего профессионального образования "ЮЖНЫЙ ФЕДЕРАЛЬНЫЙ УНИВЕРСИТЕТ" (ЮФУ) Гидрогалогениды 3-[1-(2-гидрокси-3-пиперидин-1-ил-пропил)-1н-индол-3-ил]-1-фенил-пропенона, обладающие местноанестезирующей и антиаритмической активностью
AU2011212813B2 (en) 2010-02-04 2014-10-23 Radius Health, Inc. Selective androgen receptor modulators
HUE030072T2 (en) 2010-05-12 2017-04-28 Radius Health Inc Therapeutic prescriptions
US8642632B2 (en) 2010-07-02 2014-02-04 Radius Health, Inc. Selective androgen receptor modulators
US9133182B2 (en) 2010-09-28 2015-09-15 Radius Health, Inc. Selective androgen receptor modulators
NZ744456A (en) 2012-09-26 2019-09-27 Aragon Pharmaceuticals Inc Anti-androgens for the treatment of non-metastatic castrate-resistant prostate cancer
ES3055185T3 (en) 2014-03-28 2026-02-10 Univ Duke Treatment of an estrogen receptor positive breast cancer using a selective estrogen receptor modulator
US9421264B2 (en) 2014-03-28 2016-08-23 Duke University Method of treating cancer using selective estrogen receptor modulators
MX389702B (es) 2016-06-22 2025-03-20 Ellipses Pharma Ltd Compuestos para usarse en el tratamiento de cancer de mama que expresa el receptor de androgenos (ar+).
JP7481115B2 (ja) 2017-01-05 2024-05-10 ラジウス ファーマシューティカルズ，インコーポレイテッド Ｒａｄ１９０１－２ｈｃｌの多形性形態
CN113861186B (zh) * 2021-09-10 2023-08-25 浙江师范大学 基于异恶唑取代苯甲酰胺类衍生物及抗前列腺癌药物应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ179580A (en) * 1974-12-30 1978-04-03 Mcneilab Inc 2-or 3-(w-tertiaryaminoalkyl)-thioindoles and the corresponding sulfinyl and sulfonyl analogs
US4059583A (en) * 1975-11-13 1977-11-22 Mcneil Laboratories, Incorporated Substituted indoles
GB9204365D0 (en) * 1992-02-28 1992-04-08 Pfizer Ltd Indoles
RU2337909C2 (ru) * 2002-02-01 2008-11-10 Ф.Хоффманн-Ля Рош Аг Замещенные индолы и фармацевтическая композиция, обладающая агонистической активностью в отношении альфа-1a/l адренорецептора
TW200401641A (en) * 2002-07-18 2004-02-01 Wyeth Corp 1-Heterocyclylalkyl-3-sulfonylindole or-indazole derivatives as 5-hydroxytryptamine-6 ligands

Also Published As

Publication number Publication date
AU2003301853B2 (en) 2010-02-18
AU2003301853A1 (en) 2004-06-07
TW200418793A (en) 2004-10-01
JP4643989B2 (ja) 2011-03-02
UA79504C2 (en) 2007-06-25
WO2004041782A1 (en) 2004-05-21
TWI310032B (en) 2009-05-21
PL376728A1 (pl) 2006-01-09
RS20050340A (sr) 2007-06-04
CN1714078A (zh) 2005-12-28
EP1585727A1 (de) 2005-10-19
JP2006507293A (ja) 2006-03-02
ES2344836T3 (es) 2010-09-08
RU2328484C2 (ru) 2008-07-10
NZ539657A (en) 2008-04-30
ATE469128T1 (de) 2010-06-15
RU2005117374A (ru) 2006-01-20
EP1585727B1 (de) 2010-05-26
CA2504907A1 (en) 2004-05-21
CN100391944C (zh) 2008-06-04
BR0316020A (pt) 2005-09-20

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